Asymmetric Hydrolysis of (±)-1-Acetoxy-2,3-dichloropropane with Enzymes and Microorganisms

Iriuchijima, Shinobu; Keiyu, Atsuko; Kojima, Natsuko

doi:10.1080/00021369.1982.10865271

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“…Iriuchijima et al reported the asymmetric hydrolysis of 1-acetoxy-2,3-dichloro-propane with porcine pancreatic lipase or Mucor sp. lipase, 9 and Cambou and Klibanov presented the synthesis of optically active esters of DCP by yeast lipase. 10 However, desired optical purity cannot be obtained (up to 90% ee).…”

Section: Production Of (R)-and (S)-dcp and Their Conversion Tomentioning

confidence: 99%

“…8 Esterases and lipases with stereospecific activity can be also used, but the resulting enantiomeric purity may be relatively low. 9,10 The actual needs require enantiomers with high optical purity, and the ee value should generally be >98% ee. For this purpose, simpler, more efficient, and more practical methods for preparation of chiral C3 and C4 building units have been desired.…”

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Optically active chlorohydrins as chiral C3 and C4 building units: Microbial resolution and synthetic applications

1998

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Production of highly optically active C3 and C4 chlorohydrins was developed by using the bacteria stereoselectively dehalogenating and assimilating the racemic substrate: Pseudomonas sp. and Alcaligenes sp. These bacteria stereoselectively assimilate (RS)‐2,3‐dichloro‐1‐propanol (DCP) and (RS)‐3‐chloro‐1,2‐propanediol (CPD) followed by microbial preparation of (R)‐ and (S)‐DCP, and (R)‐ and (S)‐CPD with >99% ee. A novel dehalogenating enzyme, halohydrin dehydro‐dehalogenase from one of the above strains, Alcaligenes sp. DS‐S‐7G, was applicable for preparation of optically active 1,2‐diols with 60–99% ee. Moreover, microbial resolution of C4 chlorohydrins with whole cells of Pseudomonas sp. was carried out. This resolution reaction using the resting cells gave (R)‐ and (S)‐4‐chloro‐3‐hydroxybutyrate (CHB) and (S)‐4‐chloro‐3‐hydroxybutyronitrile (BN) with >98% ee. In the case of the resting cells of Enterobacter sp., both (R)‐CHB (>99% ee) and (S)‐3‐hydroxy‐γ‐butyrolactone (95% ee) with excellent yield were obtained. Also, some typical synthetic applications using the above chiral C3 and C4 synthons were introduced: ferroelectric liquid crystals, optically active β‐blockers, and other chiral pharmaceuticals. Chirality 10:682–692, 1998. © 1998 Wiley‐Liss, Inc.

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Section: Production Of (R)-and (S)-dcp and Their Conversion Tomentioning

confidence: 99%

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confidence: 99%